Streptomycin is a well known antibiotic which was discovered by Wasksman. Streptomycin, and dihydrostreptomycin which is obtained by reduction of the aldehyde group of streptomycin are widely used as medicine in therapeutic treatment of bacterial infections. However, as streptomycin and dihydrostreptomycin become widely be used, such strains of bacteria resistant to these antibiotics have occurred, and owing to this the therapeutic effects of streptomycin and dihydrostreptomycin have considerably been reduced. The occurrence of such resistant bacteria is generally observed not only with the antibiotics of streptomycin type but also with other antibiotics such as kanamycins, lividomycins and the like. These historical facts are detailed in the general remarks as reported by Hamao Umezawa who is one of the present inventors and is a first discoverer of the mechanism of resistance of bacteria against aminoglycosidic antibiotics (H. Umezawa; "Advances in Carbohydrate Chemistry and Biochemistry" Vol. 30. page 183, Academic Press 1974). With the streptomycins, it has been found that the hydroxyl group at 3"-position of the molecule of streptomycins can be adenylated by such resistant bacteria capable of producing a streptomycin adenyltransferase and thereby 3"-O-adenylstreptomycins are formed, with a consequence that streptomycins can be inactivated in respect of their antibacterial effects (Umezawa et al; "Journal of Antibiotics" Vol. 21, page 81 (1968)). In these circumstances, we, the present inventiors, have started our study in an attempt to remove the 3"-hydroxyl group from the streptomycin molecule and thereby to eliminate the possibility of inactivation of streptomycin which would occur due to the adenylation of the 3"-hydroxy group of streptomycin so that there is provided a new derivative of streptomycin which will be active also against the bacteria resistant to streptomycin. As a result of our study, we succeeded in synthetizing 3"-deoxydihydrostreptomycin from streptomycin, and we found that this 3"-deoxydihydrostreptomycin is active against the resistant bacteria (see Japanese patent application prepublication "Kokai" No. 105154/77; and "Journal of Antibiotics" Vol. 29, 978 (1976)).
We have made our further study and have now succeeded in synthetically producing 3"-deoxystreptomycin with starting from the above-mentioned 3"-deoxydihydrostreptomycin, and we have found that the new compound, 3"-deoxystreptomycin is also active against a variety of streptomycin-resistant bacteria. Thus, we have accomplished this invention.